There's so much crap from the past that's awesome & interesting that I couldn't possibly list them all(can't even remember them all). So I'll offer a small selection of things that I do recall. As most of you know, I'm long-winded so either brace yourself or skip the post.
Once upon a time, back in the good old days of the BBS, a friend & I had 'hacked' an office building through a series of social engineering, building custom equipment, wiring the equipment into the building, etc. It was one of my favourite early complex hacks. Now that most of the businesses no longer exist, I feel it safe to share a little bit about it.
The target was an office building not far from where I went to school. This particular office building is the type that holds offices for different companies. You usually have one company that rents out an entire floor or so or occasionally a floor that is split between a couple different companies. The target building held offices for a small law firm, a document processing company, an insurance company and a company that developed, sold & supported voice mail systems. Of course, our primary focus was the voice mail system company, but being the ego-driven kids that we were(I was 11 or 12 & my friend was 16), we figured it'd be most excellent to take over the entire building and secure our place among our peers as masterminds.
The hack started out with me going to the office building every day after school for about 2 to 3 hours. This continued for a week or two until the lobby staff began to recognize me easily and relax when I was around. I started out by bringing my Atari Lynx(damn, I miss that thing) and playing it for a while and then going outside to 'play'(which was really my excuse for disappearing out of sight without anyone 'knowing' who I 'belonged' to). After a while, I decided to start bringing homework so that I could occasionally ask for a pencil sharpener or something to spark minor social interaction with the staff. Eventually, they became comfortable enough that I could just continue past the lobby into the rest of the building. At this point, I worked with the assumption that I was someone's kid, whilst carefully avoiding specifying precisely whom. Soon, I was able to convince some people to let me type on the computer and since I was young, minor annoying sounds provoked them to put me somewhere secluded where I could play on a computer without interrupting anyone's work. That is when I started hacking the local network and eventually put my friend on payroll using one of his fake IDs. Then he started coming into the office as some lowly evening janitorial staff and we started hacking away at the rest of the building.
In a couple instances, we had to use money from my friend's paycheck to buy some small equipment from Radio Shack to do things like tap phone lines, run new cabling, etc. I eventually got the idea to use an office equipment distributor to deliver new equipment to us and bill it to one of the businesses in the building. This also gave me a good excuse to introduce myself to other offices by carrying equipment between floors. The distributor would deliver it to the building, to the floor they were supposed to, where my friend would sign for it. Then we would slap a delivery label for another office on the box and I would hand carry it there, convincing them that it had been delivered to the wrong floor by accident. Finding the candy jar on every receptionist's desk, I would help myself and strike up a conversation with whomever sat there. This way I could pick up names in the office and even find a way to copy signatures("Hey Miss D., can I do something to help? I'm really good at stamping, do you want me to help stamp some stuff? I was the best stamper in grade school. Oh, is that a paper for Mr. J? I could take it to him if you want. Does it need to be stamped?" They always gave in.). They tell me to deliver a paper, I copy the signature on it on my way there. The assumption that I'd stop to bug some random person on the way meant they didn't ask what took me so long and I was rarely ever expected back.
We used information from the voice mail system company to take over some VMBs at other corporations. We were able to set up call relay on a few of the VMBs and eventually used some of those to connect to BBSs. Through some private exploits that we'd developed for a few popular BBSs, we were able to take admin on quite a few and some of them actually provided dial-out access. My friend got the idea to patch the BBS software so that file uploads would be copied to another system. Since we had access to all the companies in the office building, we used their file servers to store all the data. Since we didn't want the BBS to dial directly into the offices where we were, I used some of the VMBs as storage mediums. The BBS would, when it received a file, store the file locally and when done, dial out to a number that would always go to voice mail. It would then essentially fax the uploaded file as a voice mail and the VMB would store it until it was later retrieved by the office systems we were using as file servers. It worked quite well for almost a year but eventually some BBSs would update or the chosen VMBs would be changed or phone numbers would get reassigned(I can only imagine what someone would think when they checked their voice mail and received a fax in their ear).
It was 'rewarding' because we were able to get A LOT of useful information quite easily. We got source for some major office software, private exploits(there wasn't really a 'release' concept back then so "0day" wasn't a term we used), important business documents for some local companies, etc. The greatest thing was that, since we started this whole process by social engineering our way into the office building and eventually used that to get my friend a 'job' there, the companies themselves paid for the hack against them and we actually made a monetary profit too.
Something unrelated(but I just remembered whilst I was reliving the above); there was a time where a different friend & I were trolling a BBS whilst we hacked it. One of the BBS admins, respected by all the other admins as well as the rest of the membership as the best one there, just couldn't avoid trying to make someone look like crap in front of everyone else when they showed the slightest hint of noobishness. So we decided that the greatest distraction was to play the noob part whilst we hacked not just the BBS, but his personal machine as well. Toward the end of the conversation, we told him that we would go but we didn't want to leave it like that. So whilst I distracted him with my 'making ammends' SE work, my friend grabbed a picture of a piece of pizza, copied it w/ an office copier, messed up the paper w/ some folding & rips, copied the messed up copy and then faxed it to him. He laughed so hard and made fun of us for trying to fax a pizza and fucking up the fax machine. It literally took him like 20 minutes to realize that he'd never given out his phone number. As soon as we realized he'd figured it out, we disconnected him from the BBS, changed all the admins credentials, took over the BBS & announced to everyone that they'd been a great audience and if they had any complaints, they could call his number(at which point we publicly displayed his name, ph#, address, etc.).
It was rewarding to get revenge on an asshole who needed to be put in his place.
Yet another funny story; one time I got caught dumpster diving and I ran from the security guard(who was some distance away). I turned the corner and promptly ran into a pole, knocking the wind out of myself and falling on the ground. When the security guard caught up, he made sure that I was okay and then asked if I could describe the hobo that pushed me over. Apparently he thought the guy he was chasing was older/taller and because I was a kid, he never suspected me.